


Kissing the Boss

by raiseyourpinky



Category: Supernatural
Genre: Alternate Universe, Boss/Employee Relationship, First Kiss, Friends to Lovers, M/M, New Year's Eve, New Year's Kiss
Language: English
Status: Completed
Published: 2020-01-02
Updated: 2020-01-02
Packaged: 2021-02-27 04:00:26
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,128
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22080700
Author URL: https://archiveofourown.org/users/raiseyourpinky/pseuds/raiseyourpinky
Summary: Castiel is Dean's boss, and they both find themselves at a New Year's Eve party when Castiel confides in Dean that he's never had a New Year's Eve kiss. That is about to change tonight.
Relationships: Castiel/Dean Winchester
Comments: 4
Kudos: 102
Collections: Destiel Instagram One Shot/Art Contest - January 2020





	Kissing the Boss

**Author's Note:**

> A bit late to the party, but here it is.

Castiel had just stuffed his mouth with a cream puff when Dean walked up to him. It was just his luck for Dean to finally pay attention to him when his cheeks were full like a squirrel’s.

“Hey, boss,” Dean said, smiling his big, bright smile. It was the same one that always lit up the office every morning.

Castiel finished chewing, swallowed, and returned the smile. “Hello, Dean. Are you having fun?”

Dean rocked on his heels. “I gotta give it to Chuck. This is an awesome New Year’s Eve party. Who would have thought that genius accountant knew how to throw a party?”

Castiel chuckled. “It has been a lot of fun. I’m glad I decided to come. I usually just sit at home and rewatch  _ When Harry Met Sally _ on New Year’s Eve. But I probably shouldn’t broadcast that.”

“Actually, as your assistant for the past four years, I doubt there’s much I don’t know about you.”

That was definitely true. Castiel had let Dean see everything about him. Even the most embarrassing things. Dean made it easy. Castiel trusted him completely. “I bet you don’t know this one fact about me, though.”

Dean raised an eyebrow. “A secret? Do tell.”

Castiel smiled and shook his head, already regretting what he was about to say. “I’ve never kissed someone on New Year’s Eve.”

“What?” Dean looked genuinely shocked. “Are you serious?”

“Uh, yeah. For some reason, I’ve just never followed that tradition. When I’ve been in relationships, they just haven’t cared enough to kiss me on New Year’s. And now, I’m just too single for it to happen.” Castiel shrugged. “What are you gonna do?”

Dean rubbed the back of his neck. “Well, midnight is in two minutes. You still have time to find someone to kiss.”

“Here?” Castiel laughed. “I don’t think any of my coworkers would appreciate being kissed by me.”

“You sure about that?”

“Oh, absolutely.”

Dean grinned sideways. “Hey, Cas, would you come outside with me to get some air?”

“Sure, yeah. Let me get my coat.”

They both grabbed their coats and snuck out to the front porch just as the ten second countdown to midnight began. Fireworks sounded far away already, but they weren’t visible from Chuck’s house. 

“Three, two, one...Happy New Year!” the chant came from inside the house.

Castiel turned to Dean to wish him a Happy New Year, but found Dean’s lips instead. The kiss was soft and sweet and achingly tender. Castiel knew he should resist leaning closer--Dean was his assistant and Castiel should not cross the line that he’d wanted to cross thousands of times before. But it was impossible not to cup Dean’s cheek and lick his lips open. Dean let him in, and the kiss deepened. 

When they broke apart, Castiel realized he couldn’t stop smiling.

“Happy New Year, Cas,” Dean whispered.

“Happy New Year, Dean,” Castiel replied, licking his lips. “You...you didn’t have to do that. If you felt bad for me--”

“I know I didn’t have to do that, and I definitely didn’t feel bad for you. I wanted to do it.”

Castiel blinked. “As a New Year’s Eve tradition?”

Dean swallowed. “Not just that. But I don’t wanna get fired, so let’s pretend it was.”

Castiel’s heart was racing. “Dean. If you--do you--I mean, do you like me?”

“Heh. Yeah. I like you, Cas. Not just as my boss. I like you, as in, I’d love to take you out on a date, and keep kissing you, not just on New Year’s Eve.”

“Dean,” Castiel breathed. He’d almost forgotten how to breathe. This was huge. This was a game-changer. Dean liked him. Dean wanted to date him. How long had he felt this way? As long as Castiel? “I like you too. In the same way.”

Dean beamed. “Yeah?”

“Yeah.”

“Wow. I should have kissed you years ago.”

Castiel wrapped his arms around Dean’s waist, pulling him closer. Dean grinned, wrapping his own arms around Castiel’s neck. “You have no idea how many times I’ve wished for this moment. When I could just hold you close and kiss you.”

Dean kissed him, then. In the same gentle way he had before. “I know the feeling.”

“Maybe next year we can both stay home rewatching  _ When Harry Met Sally _ .”

Dean laughed. “That sounds like a plan, boss.”

Castiel wrinkled his nose. “I’d almost forgotten I was your boss. Almost.”

“You’re not gonna fire me if I keep kissing you, are you?”

“I might fire you if you stop.”

Dean kissed him again. And again. And again.

As much as Castiel liked it, he had to clarify. “I hope you know I was joking. I would never fire you for not kissing me, Dean. That would be unethical.”

“I know, I know.” Dean pressed his lips to Castiel’s neck, sending a shiver down Castiel’s back. “You liked that, didn’t you?”

“Mmm, yes.”

Dean pressed a trail of kisses down Castiel’s neck, leaving Castiel weak in the knees. They’d only just started doing this, but Dean was completely irresistible. Dean was the warmth Castiel needed on this cold winter night. And every other night, to be honest.

“You wanna get out of here?” Castiel blurted out without thinking. He quickly pulled back to read Dean’s face and see how much he’d screwed up. “I didn’t mean to sound so forward. I promise I don’t have any bad intentions.”

“Cas, it’s okay. I know you very well. You don’t have to walk on eggshells around me.”

“Right. You do know me. And yet, you still like me.”

“What’s not to like? You’re the most loyal person I’ve ever met. And you’re fucking gorgeous. I wish you could see yourself the way I see you.”

Castiel blushed. “I think you’re beautiful, Dean.”

“You do?” Dean looked at him with wide eyes.

“You are honest, and brave, and true, and kind, and intelligent. You’re the whole package.”

Dean pulled Castiel down to kiss him again. This time, crushing their mouths hard against each other. Gone was the gentleness from before. This kiss was rough and passionate, and Castiel couldn’t get enough. Dean kissed him like he’d been training his entire life for this moment, to give the best kiss of his life.

“Let’s say goodbye to everyone, and hit the road,” Dean said, sucking Castiel’s lower lip until Castiel let out a moan. 

“Yes, yes. I like your thinking.”

Dean let go of him, straightening the collar of Castiel’s shirt. Something he did all the time. Their own little tradition. “You still look like you just had the make-out of your life, but there’s no way to hide it.”

Castiel smiled. “I wouldn’t want to hide it if I could.”


End file.
